You mentioned some good ones yourself. We are in a European Marina and have paid a fellow scuba diver to clean off algae and check/change zincs. I don't know that they have an official work permit, but it's a pretty laid back business and I am sure it helping them support the lifestyle. They have done it for a bunch of people. Computers, yeah, lots of things.....you could do taxes for expats...skip the private charter idea, I think. Photography if you are good and have good equipment.

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Some good answers on here, day trading ( make sure u have good internet) teaching languages(less physical than being a diesel tech and we have friends in a few countries that earn well doing this) i had thought that maybe being a physical therapist (sailors are always are aching)
100 ton capt lic ,, capt 8 months in the caribbean and sail outside the hurricane zone the other 4 months
Smuggling?
Get a job at 20 where u get a pension and retire at 42?

My boyfriend is a network marketer. His tools are his computer and a cell phone or wifi signal. I am a sailmaker-canvas maker and i fix sewing machines. His office is in the forepeak and the entire aft cabin is my work space as well as the deck for large projects. We have been living and sailing on our boat from trinidad to thailand for the past 12 years and earn enough money to take care of the boat and live a very good quality of life. We are even able to put aside savings.

That is great. I would love to have a set up like that. I'm nowhere near that point yet and it is slowed even more now by a potential move for work. When I get this figured out we are going to start sailing lessons and try to make the dream a reality. Thanks for the info. It's inspiring.

Find a job that works half a year, cruise the other half. Find some bloke who does what you do and wants to work half a year and pitch the boss. Half a year is better than none.
I did it for years, bought a big boat before I could afford it and when a job finished, I took off. (I was a High-rise steel erector in Chicago).

I mean save up a big bunch of money or go for a big business idea and do all you can to make sure it pans out. I guess that's what I've been doing. I wouldn't say its the very best way, but developing the sailing skills takes time anyway. There is a reason that even the most basic US coast guard captains lic requires 360 days on the water.

The whole thing can be done for a lot less money than expected as well . Generally, there are lots of ways to econimize that don't hurt too bad, like anchoring instead of paying for marina space, you just have to find them. Also, I think someone here said it before, but there are a lot of fiberglass boats from the 70s. supply and demand makes them cheap. My first real sailboat cost $1200, 25 foot. My next, the one I own now, cost $4000, 27 foot. Don't think you'd want to take them offshore, but I feel like it takes some real learning even to get to that confidence level (for me at least). Weeklong coastal trips with a total crew of 4 or 5 are fine though and lots of fun... That's a start. Learn the skills, save some money while you do this. If you can get a passive income from some rental property or arrange a remote work setup in the meantime, even better. People have different ways of doing things, but one way is to get a boat now and start chipping away towards the dream.

Out of all these ideas about spending your life trying to get rich (by whatever means) THEN going sailing, I wonder how many who think this way ever get over 27 feet and away from the dock for more than a weekend? I had a 27 footer tied to a dock while trying to "make enough money" to go cruising up until I realized it is usually a fools dream that prevents people from going cruising. Then I sold everything and got a blue water cruiser.

i am not rich nor did i save my money for a cruising boat then go..lol....but i am gone and having the time of my life......there is a lot of merit to getting boat and refitting underway. how else will you know exactly what you want and need...guessing vs realization..........but, then, not all are like me, thank gods--if folks were all same, world would soo suck.......